# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1448837'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl2 Se'
_chemical_formula_weight         304.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.7839(6)
_cell_length_b                   7.6076(3)
_cell_length_c                   17.9304(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2425.86(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1926
_cell_measurement_theta_min      4.9920
_cell_measurement_theta_max      72.0840

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    7.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.16971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4198
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.97
_diffrn_reflns_theta_max         72.18
_reflns_number_total             1766
_reflns_number_gt                1578
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0966P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1766
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1452
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se7 Se 0.36981(2) 0.43956(6) 0.64983(3) 0.0395(3) Uani 1 1 d . . .
Cl9 Cl 0.43184(6) 0.68870(13) 0.59881(9) 0.0562(4) Uani 1 1 d . . .
Cl8 Cl 0.30672(6) 0.19481(19) 0.70815(9) 0.0617(4) Uani 1 1 d . . .
C6 C 0.3796(2) 0.3707(6) 0.4903(3) 0.0405(12) Uani 1 1 d . . .
H6 H 0.4305 0.3964 0.4949 0.049 Uiso 1 1 calc R . .
C10 C 0.4641(2) 0.3114(5) 0.6534(3) 0.0392(11) Uani 1 1 d . . .
C11 C 0.5208(2) 0.3840(7) 0.6964(3) 0.0471(13) Uani 1 1 d . . .
H11 H 0.5143 0.4914 0.7204 0.057 Uiso 1 1 calc R . .
C5 C 0.3495(3) 0.3277(6) 0.4225(3) 0.0501(13) Uani 1 1 d . . .
H5 H 0.3804 0.3236 0.3807 0.060 Uiso 1 1 calc R . .
C14 C 0.5393(3) 0.0636(6) 0.6237(4) 0.0549(15) Uani 1 1 d . . .
H14 H 0.5459 -0.0435 0.5996 0.066 Uiso 1 1 calc R . .
C2 C 0.2560(2) 0.3415(5) 0.5460(3) 0.0405(11) Uani 1 1 d . . .
H2 H 0.2246 0.3472 0.5874 0.049 Uiso 1 1 calc R . .
C4 C 0.2737(3) 0.2903(6) 0.4152(3) 0.0520(13) Uani 1 1 d . . .
H4 H 0.2540 0.2594 0.3690 0.062 Uiso 1 1 calc R . .
C3 C 0.2276(2) 0.2991(6) 0.4767(3) 0.0535(13) Uani 1 1 d . . .
H3 H 0.1765 0.2760 0.4715 0.064 Uiso 1 1 calc R . .
C1 C 0.33218(19) 0.3754(5) 0.5526(3) 0.0344(10) Uani 1 1 d . . .
C13 C 0.5965(2) 0.1333(7) 0.6654(4) 0.0540(14) Uani 1 1 d . . .
H13 H 0.6420 0.0734 0.6687 0.065 Uiso 1 1 calc R . .
C12 C 0.5879(2) 0.2911(6) 0.7026(3) 0.0553(15) Uani 1 1 d . . .
H12 H 0.6268 0.3351 0.7318 0.066 Uiso 1 1 calc R . .
C15 C 0.4719(2) 0.1522(6) 0.6174(3) 0.0488(13) Uani 1 1 d . . .
H15 H 0.4326 0.1056 0.5894 0.059 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se7 0.0308(3) 0.0500(3) 0.0377(6) -0.0060(2) -0.00054(14) 0.00104(13)
Cl9 0.0436(5) 0.0461(5) 0.0788(13) -0.0007(6) -0.0088(5) -0.0049(4)
Cl8 0.0504(6) 0.0865(9) 0.0481(11) 0.0173(8) 0.0054(5) -0.0090(5)
C6 0.0349(17) 0.050(2) 0.036(4) 0.001(2) 0.0043(17) 0.0009(15)
C10 0.0330(17) 0.046(2) 0.038(4) 0.002(2) -0.0004(15) 0.0015(15)
C11 0.039(2) 0.061(2) 0.042(4) -0.009(3) 0.0006(18) 0.0008(17)
C5 0.046(2) 0.058(2) 0.046(4) 0.001(3) 0.008(2) 0.0081(18)
C14 0.049(2) 0.051(2) 0.065(5) -0.001(3) 0.010(2) 0.0073(17)
C2 0.0312(17) 0.058(2) 0.032(3) 0.006(2) 0.0001(16) -0.0014(15)
C4 0.053(2) 0.063(2) 0.040(4) 0.001(3) -0.015(2) 0.0027(19)
C3 0.037(2) 0.067(3) 0.056(4) 0.011(3) -0.008(2) -0.0079(17)
C1 0.0334(17) 0.0428(18) 0.027(3) 0.000(2) -0.0022(15) -0.0020(13)
C13 0.037(2) 0.063(3) 0.062(4) 0.016(3) 0.010(2) 0.0074(18)
C12 0.0327(19) 0.074(3) 0.059(4) 0.009(3) -0.0064(19) -0.0025(19)
C15 0.043(2) 0.048(2) 0.055(4) -0.001(3) -0.004(2) 0.0004(16)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se7 C1 1.931(5) . ?
Se7 C10 1.941(4) . ?
Se7 Cl9 2.3761(12) . ?
Se7 Cl8 2.4123(14) . ?
C6 C5 1.368(7) . ?
C6 C1 1.400(6) . ?
C10 C15 1.380(6) . ?
C10 C11 1.385(6) . ?
C11 C12 1.390(6) . ?
C5 C4 1.385(6) . ?
C14 C13 1.369(8) . ?
C14 C15 1.380(6) . ?
C2 C3 1.379(7) . ?
C2 C1 1.384(5) . ?
C4 C3 1.376(8) . ?
C13 C12 1.383(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se7 C10 101.68(19) . . ?
C1 Se7 Cl9 90.86(12) . . ?
C10 Se7 Cl9 90.70(13) . . ?
C1 Se7 Cl8 92.01(12) . . ?
C10 Se7 Cl8 89.99(13) . . ?
Cl9 Se7 Cl8 176.85(6) . . ?
C5 C6 C1 118.7(4) . . ?
C15 C10 C11 122.6(4) . . ?
C15 C10 Se7 120.8(3) . . ?
C11 C10 Se7 116.6(3) . . ?
C10 C11 C12 117.8(4) . . ?
C6 C5 C4 120.9(5) . . ?
C13 C14 C15 120.1(5) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C4 C5 119.7(5) . . ?
C4 C3 C2 121.0(4) . . ?
C2 C1 C6 121.1(5) . . ?
C2 C1 Se7 117.6(4) . . ?
C6 C1 Se7 121.2(3) . . ?
C14 C13 C12 121.1(4) . . ?
C13 C12 C11 119.9(5) . . ?
C14 C15 C10 118.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Se7 C10 C15 -31.9(4) . . . . ?
Cl9 Se7 C10 C15 -122.9(4) . . . . ?
Cl8 Se7 C10 C15 60.1(4) . . . . ?
C1 Se7 C10 C11 151.0(4) . . . . ?
Cl9 Se7 C10 C11 60.0(4) . . . . ?
Cl8 Se7 C10 C11 -116.9(4) . . . . ?
C15 C10 C11 C12 0.2(8) . . . . ?
Se7 C10 C11 C12 177.2(4) . . . . ?
C1 C6 C5 C4 0.3(7) . . . . ?
C6 C5 C4 C3 1.0(7) . . . . ?
C5 C4 C3 C2 -1.2(7) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C3 C2 C1 C6 1.4(6) . . . . ?
C3 C2 C1 Se7 178.6(3) . . . . ?
C5 C6 C1 C2 -1.5(7) . . . . ?
C5 C6 C1 Se7 -178.7(3) . . . . ?
C10 Se7 C1 C2 139.6(3) . . . . ?
Cl9 Se7 C1 C2 -129.5(3) . . . . ?
Cl8 Se7 C1 C2 49.2(3) . . . . ?
C10 Se7 C1 C6 -43.1(4) . . . . ?
Cl9 Se7 C1 C6 47.8(3) . . . . ?
Cl8 Se7 C1 C6 -133.5(3) . . . . ?
C15 C14 C13 C12 0.9(9) . . . . ?
C14 C13 C12 C11 -1.7(9) . . . . ?
C10 C11 C12 C13 1.2(8) . . . . ?
C13 C14 C15 C10 0.4(9) . . . . ?
C11 C10 C15 C14 -1.0(8) . . . . ?
Se7 C10 C15 C14 -177.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.740
_diffrn_reflns_theta_full        72.18
_diffrn_measured_fraction_theta_full 0.739
_refine_diff_density_max         0.426
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.145
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1448838'
_audit_update_record             
;
2016-01-21 deposited with the CCDC.
2016-07-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Cl2 O P'
_chemical_formula_weight         375.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.65192(16)
_cell_length_b                   18.5698(6)
_cell_length_c                   19.0554(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.338(3)
_cell_angle_gamma                90.00
_cell_volume                     1991.28(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2877
_cell_measurement_theta_min      4.6550
_cell_measurement_theta_max      72.0430

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    3.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54404
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7241
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         72.24
_reflns_number_total             3823
_reflns_number_gt                3225
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1491P)²+5.4760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3823
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.2604
_refine_ls_wR_factor_gt          0.2532
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 1.11563(17) 0.62014(6) 0.68610(5) 0.0325(3) Uani 1 1 d . . .
Cl1 Cl 1.0033(3) 0.55110(7) 0.81610(6) 0.0604(4) Uani 1 1 d . . .
O1 O 1.3736(5) 0.62997(18) 0.70655(19) 0.0469(8) Uani 1 1 d . . .
C1 C 1.0396(8) 0.5336(2) 0.6469(2) 0.0364(9) Uani 1 1 d . . .
Cl2 Cl 0.8026(3) 0.69877(8) 0.87752(6) 0.0639(5) Uani 1 1 d . . .
C2 C 0.8357(8) 0.4949(3) 0.6560(3) 0.0452(11) Uani 1 1 d . . .
H2 H 0.7269 0.5124 0.6856 0.054 Uiso 1 1 calc R . .
C3 C 0.7932(10) 0.4298(3) 0.6209(3) 0.0536(12) Uani 1 1 d . . .
H3 H 0.6574 0.4034 0.6279 0.064 Uiso 1 1 calc R . .
C4 C 0.9509(10) 0.4039(3) 0.5760(3) 0.0578(14) Uani 1 1 d . . .
H4 H 0.9219 0.3604 0.5526 0.069 Uiso 1 1 calc R . .
C5 C 1.1521(11) 0.4432(3) 0.5661(3) 0.0620(15) Uani 1 1 d . . .
H5 H 1.2579 0.4264 0.5352 0.074 Uiso 1 1 calc R . .
C6 C 1.1975(9) 0.5072(3) 0.6015(3) 0.0489(11) Uani 1 1 d . . .
H6 H 1.3350 0.5328 0.5950 0.059 Uiso 1 1 calc R . .
C7 C 1.0038(7) 0.6837(2) 0.6195(2) 0.0341(9) Uani 1 1 d . . .
C8 C 0.7785(8) 0.6771(3) 0.5838(2) 0.0410(10) Uani 1 1 d . . .
H8 H 0.6769 0.6409 0.5963 0.049 Uiso 1 1 calc R . .
C9 C 0.7047(9) 0.7241(3) 0.5298(3) 0.0504(12) Uani 1 1 d . . .
H9 H 0.5550 0.7190 0.5056 0.061 Uiso 1 1 calc R . .
C10 C 0.8553(11) 0.7787(3) 0.5121(3) 0.0585(14) Uani 1 1 d . . .
H10 H 0.8051 0.8108 0.4763 0.070 Uiso 1 1 calc R . .
C11 C 1.0769(11) 0.7859(3) 0.5467(3) 0.0556(13) Uani 1 1 d . . .
H11 H 1.1771 0.8225 0.5342 0.067 Uiso 1 1 calc R . .
C12 C 1.1532(8) 0.7380(3) 0.6010(3) 0.0436(10) Uani 1 1 d . . .
H12 H 1.3041 0.7427 0.6246 0.052 Uiso 1 1 calc R . .
C13 C 0.9356(8) 0.6291(2) 0.7615(2) 0.0356(9) Uani 1 1 d . . .
H13 H 0.7663 0.6293 0.7448 0.043 Uiso 1 1 calc R . .
C14 C 0.9970(8) 0.6963(3) 0.8066(2) 0.0410(10) Uani 1 1 d . . .
H14 H 1.1607 0.6911 0.8279 0.049 Uiso 1 1 calc R . .
C15 C 0.9783(8) 0.7668(2) 0.7687(2) 0.0391(10) Uani 1 1 d . . .
C16 C 0.7737(8) 0.7876(3) 0.7281(3) 0.0457(11) Uani 1 1 d . . .
H16 H 0.6424 0.7572 0.7236 0.055 Uiso 1 1 calc R . .
C17 C 0.7645(11) 0.8534(3) 0.6943(3) 0.0586(14) Uani 1 1 d . . .
H17 H 0.6288 0.8666 0.6658 0.070 Uiso 1 1 calc R . .
C18 C 0.9567(13) 0.8998(3) 0.7027(4) 0.0657(16) Uani 1 1 d . . .
H18 H 0.9493 0.9444 0.6804 0.079 Uiso 1 1 calc R . .
C19 C 1.1589(12) 0.8799(3) 0.7440(4) 0.0625(15) Uani 1 1 d . . .
H19 H 1.2874 0.9113 0.7500 0.075 Uiso 1 1 calc R . .
C20 C 1.1714(9) 0.8138(3) 0.7764(3) 0.0504(12) Uani 1 1 d . . .
H20 H 1.3094 0.8002 0.8036 0.061 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0286(6) 0.0345(6) 0.0344(6) -0.0025(4) 0.0024(4) 0.0008(4)
Cl1 0.0907(10) 0.0483(7) 0.0420(7) 0.0099(5) 0.0058(6) 0.0037(6)
O1 0.0310(16) 0.0519(19) 0.057(2) -0.0036(16) -0.0013(14) -0.0001(13)
C1 0.037(2) 0.034(2) 0.037(2) -0.0015(17) -0.0002(17) 0.0045(17)
Cl2 0.0842(10) 0.0715(9) 0.0389(7) -0.0093(6) 0.0215(6) -0.0015(7)
C2 0.042(2) 0.042(2) 0.052(3) -0.005(2) 0.007(2) -0.0022(19)
C3 0.055(3) 0.043(3) 0.061(3) -0.004(2) 0.002(2) -0.009(2)
C4 0.066(3) 0.040(3) 0.064(3) -0.015(2) -0.006(3) 0.005(2)
C5 0.063(3) 0.060(3) 0.064(3) -0.021(3) 0.012(3) 0.011(3)
C6 0.047(3) 0.048(3) 0.053(3) -0.009(2) 0.012(2) 0.002(2)
C7 0.035(2) 0.036(2) 0.033(2) -0.0018(16) 0.0088(16) 0.0023(16)
C8 0.041(2) 0.044(2) 0.038(2) -0.0004(18) 0.0047(18) 0.0023(19)
C9 0.047(3) 0.064(3) 0.040(2) 0.000(2) 0.001(2) 0.011(2)
C10 0.077(4) 0.059(3) 0.040(3) 0.012(2) 0.011(2) 0.017(3)
C11 0.068(3) 0.048(3) 0.053(3) 0.009(2) 0.020(3) -0.005(2)
C12 0.042(2) 0.045(2) 0.044(2) -0.001(2) 0.0097(19) -0.0020(19)
C13 0.038(2) 0.038(2) 0.0313(19) 0.0008(17) 0.0028(16) 0.0000(17)
C14 0.040(2) 0.049(3) 0.034(2) -0.0103(19) 0.0019(17) -0.0008(19)
C15 0.041(2) 0.041(2) 0.036(2) -0.0115(18) 0.0078(17) 0.0003(18)
C16 0.040(2) 0.048(3) 0.049(3) -0.009(2) 0.005(2) 0.003(2)
C17 0.060(3) 0.058(3) 0.059(3) 0.000(3) 0.009(3) 0.016(3)
C18 0.086(4) 0.044(3) 0.071(4) -0.001(3) 0.029(3) 0.007(3)
C19 0.068(4) 0.046(3) 0.076(4) -0.017(3) 0.023(3) -0.016(3)
C20 0.044(3) 0.052(3) 0.055(3) -0.019(2) 0.008(2) -0.006(2)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.485(3) . ?
P1 C7 1.804(4) . ?
P1 C1 1.806(4) . ?
P1 C13 1.844(4) . ?
Cl1 C13 1.803(4) . ?
C1 C2 1.382(6) . ?
C1 C6 1.390(6) . ?
Cl2 C14 1.819(5) . ?
C2 C3 1.393(7) . ?
C3 C4 1.378(8) . ?
C4 C5 1.379(9) . ?
C5 C6 1.379(8) . ?
C7 C12 1.382(6) . ?
C7 C8 1.392(6) . ?
C8 C9 1.382(7) . ?
C9 C10 1.386(8) . ?
C10 C11 1.367(8) . ?
C11 C12 1.402(7) . ?
C13 C14 1.537(6) . ?
C14 C15 1.495(7) . ?
C15 C16 1.385(7) . ?
C15 C20 1.394(7) . ?
C16 C17 1.380(8) . ?
C17 C18 1.384(9) . ?
C18 C19 1.376(10) . ?
C19 C20 1.374(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C7 112.1(2) . . ?
O1 P1 C1 114.1(2) . . ?
C7 P1 C1 103.7(2) . . ?
O1 P1 C13 112.6(2) . . ?
C7 P1 C13 107.88(19) . . ?
C1 P1 C13 105.9(2) . . ?
C2 C1 C6 119.0(4) . . ?
C2 C1 P1 125.4(3) . . ?
C6 C1 P1 115.4(4) . . ?
C1 C2 C3 120.0(5) . . ?
C4 C3 C2 120.6(5) . . ?
C3 C4 C5 119.4(5) . . ?
C4 C5 C6 120.4(5) . . ?
C5 C6 C1 120.6(5) . . ?
C12 C7 C8 119.5(4) . . ?
C12 C7 P1 118.3(3) . . ?
C8 C7 P1 122.1(3) . . ?
C9 C8 C7 120.5(5) . . ?
C8 C9 C10 119.5(5) . . ?
C11 C10 C9 120.7(5) . . ?
C10 C11 C12 120.0(5) . . ?
C7 C12 C11 119.9(5) . . ?
C14 C13 Cl1 107.7(3) . . ?
C14 C13 P1 113.4(3) . . ?
Cl1 C13 P1 105.9(2) . . ?
C15 C14 C13 116.0(4) . . ?
C15 C14 Cl2 108.4(3) . . ?
C13 C14 Cl2 108.4(3) . . ?
C16 C15 C20 119.3(5) . . ?
C16 C15 C14 122.2(4) . . ?
C20 C15 C14 118.5(4) . . ?
C17 C16 C15 120.1(5) . . ?
C16 C17 C18 120.1(6) . . ?
C19 C18 C17 120.0(6) . . ?
C20 C19 C18 120.1(5) . . ?
C19 C20 C15 120.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        72.24
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         1.681
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.173




